Why you should write about the shit that scares you

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I’ve written close to a million words or so, at this point.

And I still want to throw up a little bit with everything I write.

A lot of those words have been about suffering and the human condition.

(And relationships and sex, too.)

But inherent in almost all of my writing is this notion that I’m writing about things that scare the shit out of me.

I’ve felt the most uncomfortable I’ve ever felt in my life publishing some of the things I’ve written.

Just words, right?

This post is about how writing in that way helps you to connect with readers.

(And this advice can relate to just about anything: PR, an email, a dumb fucking research paper for school, etc. If you don’t care about the subject-matter, neither will your reader(s).)

And that, by refusing to share your story (even the shitty parts), you’re robbing them of that opportunity to connect with you.

You can read the entire article 7ish minute article in full on my website here.

Or you can just read it after the break, in this email.

— Mike Kilcoyne

I was on the phone with my grandma and she was crying because my uncle had been diagnosed with pancreatic cancer and was going to die in the next 6-12 months.

I was exhausted, because I’d been downstairs in a massive conference center in Chicago and had been out in the sun for approximately six-minutes.

Moments before, we’d crawled upstairs like a bunch of cave-trolls and started to peak at the light through the hotel bar’s massive windows when I got a call from my mom.

I left the table to take the call and I assumed it was just another routine check-in because we hadn’t spoken in a few days.

She explains that my uncle has pancreatic cancer and that the outlook isn’t great.

I took the call in the center bridge connecting the two massive parts of the hotel and I’ve got my St Patty’s Day green pants on and a graphic t-shirt and I’m just looking out the window at Chicago’s river walk.

And I’m just contemplating how small the world feels right now.

My mom had suggested I call my grandma, and so I did.

“Hey, I got the news…” and it was shitty.

I felt close-ish to my uncle, but not as close as I could’ve been had I called him more often or actually lived in Kentucky (where that side of my family lived).

And so, she told me about my uncle’s diagnosis and how they were at the hospital and howe she felt and then she started to cry.

That was the first time I’d heard her cry since her husband had passed away.

Then I started to cry, too.

“Shit…” I said. “This sucks.”

My eloquence is the first thing to go.

And then we said our goodbyes, and I continued pondering for a few more minutes.

I got up, wiped the tears off of my face and rejoined my table as if nothing had ever happened.

The first thing I tried to do was laugh.

If it’s not giving you pause, think about it some more.

It had been saved in my drafts for about 3 or 4 months before I ever considered publishing it, let alone sharing it with friends on Facebook.

It probably would’ve just floated away into obscurity had I not put it on my wall.

The article was entitled: “On being 25 and a virgin.”

I wrote it once.

And then I rewrote it.

And then I threw it out.

And then I kept it in drafts for a few more weeks.

One day, I finally said, fuck it and hit publish.

I wanted to throw up.

A few days later, I had a call with a recruiter for some bullshit company that I never had any desire to work at.

I don’t remember the name of the company, but I do remember the reaction that the recruiter had over the phone when she read the title of my latest article.

Wow! Okay…” and then she acted as if she hadn’t read it.

(What a fucking wimp, right? She sounded like she was around 4,000 years old and still watched Jeopardy every night.)

The rest of the conversation was deeply forgettable because, again, I had no interest in working for the company.

I just wanted to write.

A colleague of mine from a while ago once asked me, “does your employer, or anyone you know read the stuff you write?”

And I had to respond in the affirmative, because just about everyone I knew had probably read some of the shit that I’d written.

“Wow,” he said. “That’s insane.”

“No, not anymore,” I said.

We’re all secretly voyeurs.

“Wait, was that the polyamorous relationship?” she asked.

And I nodded my head.

“Oh, yeah, I read about that one already,” she said, and I blushed.

Because even in spite of the fact that it might seem effortless for me to share these things with complete strangers, a lot of the wounds are still pretty fresh.

But my secrets and my stories, that’s my voice.

And I honestly can’t think of anything else that I’d be even remotely qualified to write about.

(And certainly not in a way that people might find appealing.)

There are plenty of writers who simply educate.

Some of them I admire and follow.

Tim Ferriss is one of them, even though he’s secretly an asshole, too.

Their uniqueness exists solely in the fact that they write and educate.

But deep down, beyond their long listicles or diatribes on how Babe Ruth’s Afternoon Shit Routine Can Change Your Life, most of them have stories.

(And every now and then, you’ll be able to find those stories.)

And most of them are too afraid to tell those stories, because that’s not what their writing is about.

(And it probably feels narcissistic because it is.)

But we’re all secretly voyeuristic.

We want to know the deep, dirty secrets that people don’t like to share.

We want to read this things anonymously from our dirty chaise lounge in our uncomfortably small living room.

And yet, most writers will cheat their readers out of those inner-most secrets, because writing about those things is only for insane people.

But reading (and writing) is all about human-connection.

If you can find a way to make somebody go, ugh, and feel like they’d been hit in the gut, then you’re connecting with people.

Writing should compel people to share their deep, dark secrets with you, too.

“My girlfriend abuses me and I don’t know what to do,” they’ll write you.

“I’m sorry,” I’ll write back.

And now I’ve gotten just a tiny glimpse into their world.

And it’s dark, too.

There’s always a light.

She was speaking from the heart and it was better than anything I’d ever written and certainly any speech I’d ever delivered.

Because most of the time I mumble, say umm, read off a piece of a paper

I can’t remember exactly what she said, but I think it was something along the lines of, this is just one moment. Most of the other ones were great. Let’s remember his life not by how it ended but by how he lived.

Her impassioned speech was being delivered in front of a bunch of crying adults at my uncle’s graveside ceremony.

Everyone was crying because death sucks.

People who I’d never seen cry before in my life.

This moment sucks, but life is okay.

I was the most alone I’d ever felt in my entire life.

Blame it on the alcohol, my anxiety or the fact that I’d never traveled alone before, but I felt like death and like dying.

I was in a hotel in Frankfurt and I just wanted to go home but my flight wasn’t for another day or two.

And so, I’d be thrust awake by anxious thoughts after maybe 15-minutes of shut-eye.

Rinse, repeat for the entire rest of my 36+ hours there.

(And if you’ve read my stuff before, you’ve probably seen 3 or 4 different variations of this story.)

The only human contact I’d had in the last few days was: A. The ICE train ticket-taker and B. The clerk at the front-desk.

And so, I was tired.

And I’d imagine that that’s what drives people to suicide more than anything else: they’re not sleeping anymore, they’re always anxious and worried and they feel lost and hopeless.

Exhaustion.

And so, I had about 36-hours left before my flight back to New York and back to my friends and family and I felt like giving up.

But also like, if I just stuck it out for another 36+ hours, everything would be fine.

(Because my life, for the most part, was plenty cushy.)

So, I did.

I ate shitty hotel food; drowned myself with booze at night; slept my requisite 30+ minutes and then eventually made it to the airport without first throwing myself the 5+ floors into the hotel’s massive, open atrium.

Splat, I thought.

I got to my flight about 4-hours early because, again, I couldn’t sleep.

Eventually, I boarded.

As soon as I plopped my ass down into my uncomfortably tight row of seats, I felt lighter than I’d ever felt in days and even weeks.

Home free, I thought.

And then I dozed off, and got the best sleep I’d ever gotten in, I don’t know, weeks.